Rossi-Ashton, James A, Clarke, Aimee K, Donald, James R orcid.org/0000-0002-2176-4902 et al. (4 more authors) (2020) Iridium Catalyzed Enantioselective Intermolecular Indole C2-Allylation. Angewandte Chemie International Edition. pp. 7598-7604. ISSN 1433-7851
Abstract
The enantioselective intermolecular C2-allylation of 3-substituted indoles is reported for the first time. This directing group-free approach relies on a chiral Ir-(P, olefin) complex and Mg(ClO4)2 Lewis acid catalyst system to promote allylic substitution, providing the C2-allylated products in typically high yields (40-99%) and enantioselectivities (83-99% ee) with excellent regiocontrol. Experimental studies and DFT calculations suggest that the reaction proceeds via direct C2-allylation, rather than C3-allylation followed by in situ migration. Steric congestion at the indole-C3 position and improved π-π stacking interactions have been identified as major contributors to the C2-selectivity.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EPSRC EP/R013748/1 |
Depositing User: | Pure (York) |
Date Deposited: | 26 Feb 2020 09:10 |
Last Modified: | 26 Nov 2024 00:45 |
Published Version: | https://doi.org/10.1002/anie.202001956 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/anie.202001956 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:157699 |
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